Boron trifluoride → 1-(6-Bromonaphthalen-2-yl)ethanone

Participants

Reaction Steps

The compound of formula (II), 2-bromonaphthalene, is reacted with about 1 to 4 molar equivalents, preferably about 1.5 molar equivalents, of an acetyl halide, preferably acetyl chloride, in the presence of about 0.1 to 15 molar equivalents, preferably about 5 to 7 molar equivalents, of a Friedel-Crafts catalyst such as ferric chloride, zinc dichloride, tin tetrachloride, boron trifluoride or preferably aluminum trichloride, in a suitable solvent such as nitromethane, carbon disulphide, acetonitrile, methylene chloride or preferably nitrobenzene. The reaction is conducted at a temperature of about 25°-100° C., preferably about 50° C., for about 1-24 hours, preferably about 4 hours, giving the compound of formula (III), 2-bromo-6-acetylnaphthalene. When the reaction is substantially complete, the product of formula (III) is isolated by conventional means, for example crystallization.

Provenance & Evidence